


Dirty Dealings

by salppho



Category: Hazbin Hotel (Web Series)
Genre: Abusive Valentino (Hazbin Hotel), Aromantic Angel Dust (Hazbin Hotel), Content Warning: Conversion Therapy, Gen, I Haven't Been Here In Months & Forgot How To Tag Stuff Here, I'm Sorry If I Missed Anything, Intended Italian Mafia Accuracy, Mentioned Valentino (Hazbin Hotel), More Comprehensive Content Warnings In The Beginning Note, Sex Worker Angel Dust (Hazbin Hotel)
Language: English
Status: Completed
Published: 2020-10-02
Updated: 2020-10-02
Packaged: 2021-03-08 04:08:24
Rating: Mature
Warnings: Major Character Death
Chapters: 1
Words: 1,947
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26769265
Author URL: https://archiveofourown.org/users/salppho/pseuds/salppho
Summary: A prequel minific I wrote for my Angel Dust rp blog on tumblr. Events span from Angel's birth to the rough beginning of the Hazbin Hotel pilot. Please give me kudos for absolutely NAILING that word count ( Angel died in 1947 ) because it was COMPLETELY UNINTENDED.
Kudos: 4





	Dirty Dealings

**Author's Note:**

> CONTENT WARNINGS: ( each at least remotely implied, but none very graphic ) homophobia, violence, gang activity, grooming, murder, drug use, alcoholism, sexual abuse, domestic abuse, toxic masculinity
> 
> DISCLAIMER: This is a personal headcanon exposé of one of the many ways Angel could have experienced his waking life. Until his life is revealed in more detail, this is the background my portrayal ( on tumblr ) will be based upon. I did my best to muse his world with as much historical accuracy as possible, but there may be some mistakes. This will also be subject to change the more I develop him ( on tumblr ), & include some personal experiences of mine as well.
> 
> For A03's sake, consider this a oneshot prologue.

Anthony was born into the Chicago Outfit in the early 1900s. He was the first out of a pair of fraternal twins, the other being his younger sister, Molly. Having been born to impoverished Italian immigrant parents led to a lot of stress and strife throughout his childhood, which often subsequented to him taking on a lot of housework as well as a joint parental roles to Molly with his little brother Arackniss. Nonetheless, (aside from the casual reprimands dealt by his father for taking on stereotypically feminine roles around the household) Anthony’s positive attitude, contagious laughter, & practical jokes to entertain his siblings made for a more or less enjoyable childhood for him... until Prohibition sparked a demand for underground alcohol production, a niche criminal market that spring-boarded Mafia influence in the Big Apple.

As the family got increasingly busy & turf / business wars started breaking out with more blood & ferocity, Anthony's father Henry started expecting his participation, soon grooming him into violence desensitization so he may take over as the next head of the family. What started out as innocently helping his parents brew moonshine turned into learning how to use & clean guns so he may join the fight to secure his family's power & influence over the surrounding areas. The young boy started facing more severe consequences for taking on domestic jobs his father preferred Molly do, spending too much time with his mother, & being too physically affectionate with his male friends to be considered casually acceptable. Most severely, an innocent comment about preferring to marry another boy rather than a girl, only for his mother to fearfully grab him by the shoulders & make him swear never to speak that way again. From then on, Anthony could only achieve approval from his father when he was violent, ruthless, & his once harmless pranks turned sadistic & dangerous... but that still wasn’t enough.

School & mafia life became even more of an impossible juggling act, causing Anthony to drop out rather early in his education to pursue other life skills, including his formal ritualistic induction into the mafia: committing a murder & swearing to follow Sicilian adopted codes of conduct. Little Anthony had spent too much time sneaking out of his bedroom window for nightly adventures with his friends, sharing innocent kisses under the stars, & making promises a young boy couldn’t be making with another boy. In a heavy-hearted attempt to torture the “ filly ” out of his boy, Henry started preaching the certain damnation of “men who layed with men” & the true meaning of men kissing other men in the mafia. The little boy’s world shattered upon misinterpreting the promise to kill... & his young, naïve, & broken heart vowed to never kiss a man again as his father forced his paramour down the sights of his Colt M1911A1, the cold metal much too heavy for loving hands that would much rather be holding another.

By his early adulthood, Anthony found himself in full swing amidst the Castellammarese War. He’d shut off his heart, earned the reputation of a loose canon, & jumped every opportunity to hunt down a traitorous Mafioso so he could seal their demise with the forbidden kiss by which he betrayed himself. The chaotic reincarnation of Judas devoted all but every waking moment towards working with his father to fight for the family alongside big names such as Colosimo, Torrio, & Capone. After years of building up his reputation as a cold-hearted executioner of traitors, Anthony secured his infamy during the 1929 Saint Valentine's Day Massacre, having been one of four gunmen sent to murder key members of the North Side Gang. After proving his prowess, he became a trusted member of Capone’s “American Boys” & finally made his father proud.

As Anthony approached marrying age & started facing greater pressures to carry on the family name, he started becoming more painfully self aware of his sexuality, particularly the guaranteed violence (& potential death) he'd doubtlessly be subjected to if he ever acted upon his desires without subsequent murder. His most high stakes & violent years behind him, the lavish reward of higher living & increased quiet led him reminiscing about his childhood before being indited into the mob. Friends he remembered fondly, boys he crushed on, a rampant, childish jealousy of his best childhood friend’s first girlfriend, the murder of his first love whose face he could no longer remember, whose sensation he could no longer feel despite the number of times he searched for it again.

Anthony’s only option, therefore, was to conform to family expectations & start opening himself up to dating women, something that continuously failed to appeal to him. He struggled with the public façade he was forced to cultivate, but the pain was little to nothing that could be solved with some alcohol, the occasional recreational drug, & the more frequent murder of opposing mobsters that as much as looked at him poorly.

After a few years of struggle & failed attempts to bed women, Anthony managed to land himself a fiancé who was less interested in sex with him than he was with her. It was an ideal companionship, & the two married to satisfy their respective familial troubles. It was something neither of them wanted, but it kept suspicious mouths shut, allowed them to live their lives without pressure from one another to commit, & perform a much needed rewriting of their sexual prowess. They even negotiated blaming a lack of children to "bad luck" & reassured their families they’d “keep trying”. With the transition of power from Capone to Nicci & Ricca, Anthony busied himself with training recruits from the Forty-Two Gang, a notoriously violent youth gang. Despite their criminal circumstances, he felt content playing Mafia house with his newly adopted murderous children. It reminded him of a simpler time before the Chicago Outfit invaded his peaceful domestic life with his mother & siblings. Eventually, his understudies would rule the mafia in his place, as organized leadership never personally appealed to him.

Mediocre marital bliss then came to a screeching halt when Anthony found himself at the premier of The Glass Menagerie, a memory play written by the same playwright who once went by the name The Gentleman Caller. The last thing he wanted to do was sit through a live performance, blaming it on impatience & restlessness in place of a desire for all the men of the theater to have their eyes on him rather than a silver screen starlet. Expecting the evening to be little more than torturous, he caught the gaze of another man in line who looked at him not in the way that’d earn his Tommy gun to his face, but in a way Anthony felt genuinely seen for the longest time in his life. He finally remembered the giddiness of young women & girls catching the glance of their paramours, the lengths boys & men alike went to ascertain parental permission to pursue their daughters. In a moment, he made an intimate connection that revived a desire he’d long buried into the lost catacombs of his soul.

And it felt dangerous. And exciting. If not for his wife tugging his arm, the two of them could’ve stayed staring at each other from across the block. As they grew closer & closer, doubling lines from either side of the street finally meeting at the center pair of ticket-masters, Anthony felt his heart beating more & more violently. When he finally saw the whites of his eyes, he felt like he could risk his entire life’s ambitions & reputation to kiss him right there, run him across town, & spend the rest of his life in obscurity. A lifetime of disgust, shame, violence, & smothered self-loathing wiped away by a kind smile that spoke a language meant only for him. With the blessing of his wife, Anthony stayed behind to chat with the man as she went & held his seat.

As the lights in the theater went off, Anthony felt the urge to scream as the man touched his hand. The two then promptly left the world behind & fled somewhere private where their lips could hold each other & hands could wander without being seen. In spite of the hunger & the daze, most of their energies were nonetheless terrified. Hands too shaky to part clothing, peripheral senses still too alert to truly focus on one another. They stayed in the dark for what felt like hours, until the scuffling of intermission outside all but threw them from each other’s bodies to vanquish themselves into the crowd, never to see one another again.

And Anthony went mad. As if independent from his soul, his empty shell returned to his wife & dissociated to the performance. He watched with a thousand yard stare as his mortal being went through the motions of his daily life. His heart & soul stayed in the dark with his Gentleman Caller, & it became all to clear that he’d never leave his side, that moment.

As if he wasn’t already the wielder of a violent reputation, Anthony started taking his frustrations out on the world. When the drugs weren’t enough, he started to make noise. When the alcohol couldn’t numb him enough to the ghosting memories of his lost lover, he turned on his wife, the only other person in the world who could’ve understood him. Nothing was enough anymore. Nothing could ever be enough. Before his fellow American Boys could begrudgingly slay him for putting the Mafia at risk, he was found dead of an overdose of PCP, a.k.a. Angel Dust.

Anthony’s rage followed him into Hell, but he no longer need suffer consequence. He named himself after the miracle drug that set him free & rose Cain upon the Pentagram until he was proposed an offer he couldn’t refuse: the opportunity to make his wildest dreams come true, the opportunity & platform to have every denizen of hell crave & worship his form & body. The freedom was fun. The wild sex was fun. The ability of his new body to tolerate greater amounts of his favorite poison & sustain a much more rewarding high, was fun. His current reputation as a violently sexual powerhouse was one he’d always dreamed of possessing.

But his greed & exponentially growing ego got the best of him. He traded his independence for a contract that quickly grew into his reputation as Hell’s most famous porn star under Valentino’s guidance. He didn’t care. His family’s wishes no longer had any hold over him in Hell. For the first time since his rendezvous at the theater, he felt free & genuine to pursue all his interests in the studio. He took care of his coworkers, expanded his wardrobe, dabbled in more drag & became a master of all things beauty & care. He discovered a love of sex work that he never could’ve pursued in his waking life, & his natural affinity for it only helped boost his stardom & reputation.

Angel, the Spider in the Kinky Boots, was thriving... until the Overlord started exerting more & more power over him. Being famous, loved, & adored for the very things that would’ve fatally condemned him in life was more than a dream come true, but Heaven in Hell to him. Had he let himself come clean with his vulnerabilities, he could’ve even fallen in love again... but slowly, & surely… the honeymoon periods came few & far in between before being all but over. Angel achieved his fame, but with the cost of falling deeper & deeper unto Valentino’s control. The freedom he once reasserted for himself faded further & further into his memory until it was no longer his.

So he started to fight. Volatile mumbles under his breath became vague Instagram posts. Tolerating the moth’s sexual urges became resisting him. Trashing his room in frustration became setting up his new residence in the Hazbin Hotel.


End file.
